Dimethylformamide → 6-Fluoro-3,3-dimethylisoindolin-1-one

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	HCID 83712564	HCID 83712564	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	6-Fluoro-3,3-dimethylisoindolin-1-one	HCID 71744000	8.6%

Reaction Conditions

Temperature	130 °C

Reaction Steps

A mixture of 1-(2-bromo-4-fluoro-phenyl)-1-methyl-ethylamine (1.5 g, 6.52 mmol), Pd(dppf)Cl2 (0.15 g), DIPEA (2.52 g, 19.6 mmol) in DMF (20 mL) was stirred in an autoclave under 2 MPa of CO (g) at 130° C. for 16 hours. After it was cooled to room temperature, the reaction mixture was diluted with EtOAc (300 mL). The organic layer was washed with brine, filtered, and concentrated under reduced pressure to give a crude product which was purified by chromatography to give the title compound (100 mg, yield 8.6%) as a brown solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133158B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-0b967671d7114d9e8a398b900a9cc43a
Source note	uspto-grants-2015_09